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05/25/2024  ± 1 day
All listings in Mississauga

Great sailboat rentals near Mississauga, Ontario.

Page 1 of 111 listings

27 Foot Sailboat for a Day of Fun in the Sun in Toronto
Sailing in Toronto · 6 guests

27 Foot Sailboat for a Day of Fun in the Sun in Toronto

5.0
$55person
35ft C&C 35 Sailboat in Toronto
Sailing in Etobicoke · 6 guests

35ft C&C 35 Sailboat in Toronto

5.0
$182hour
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$73person
A Tropical Experience on a Massive Sailing Trimaran
Sailing in Toronto · 12 guests

A Tropical Experience on a Massive Sailing Trimaran

4.9
$327hour
Beautiful Trimaran for 10 People in Toronto
Sailing in Toronto · 12 guests

Beautiful Trimaran for 10 People in Toronto

5.0
$291hour
Discover the Magic of Sailing: Private Tours for Every Occasion
Sailing in Scarborough · 4 guests

Discover the Magic of Sailing: Private Tours for Every Occasion

5.0
$73hour
Fountain Pajot Astrea Luxury 42' Catamaran for Charter
Sailing in Toronto · 18 guests

Fountain Pajot Astrea Luxury 42' Catamaran for Charter

5.0
$1,100-$1,250hour
Stylish & Spacious‼️ Enjoy Toronto's One of a Kind 44ft Bayliner!
Events in Toronto · 15 guests

Stylish & Spacious‼️ Enjoy Toronto's One of a Kind 44ft Bayliner!

5.0
$364hour
38' Sailing Yacht in Toronto, Ontario
Sailing in Toronto · 8 guests

38' Sailing Yacht in Toronto, Ontario

New
$400hour
28' Sailboat for 5 guests in Toronto
Sailing in Toronto · 5 guests

28' Sailboat for 5 guests in Toronto

New
$235hour
41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests
Sailing in Toronto · 12 guests

41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests

New
$435hour

Sailing Reviews in Mississauga

  1. TR

    Timothy

    35ft C&C 35 Sailboat in Toronto

    Peter and the Restless are a wonderful experience. He’s a very knowledgeable and professional individual as well as fun and engaging. The Restless is a great boat and the trip was well worth it! Can’t recommend Peter and his experience more highly.

  2. CE

    Celine

    35ft C&C 35 Sailboat in Toronto

    We had the most amazing time with Peter. I booked this trip for my fiancé and I’s engagement photoshoot. Peter was very welcoming and helpful throughout the trip. 10/10 would recommend it for everyone! Thank you Peter!

  3. James

    James

    35ft C&C 35 Sailboat in Toronto

    Peter is a great skipper and host. We thoroughly enjoyed the trip. His boat was spotless and well maintained. He was very knowledgeable about the area and his sailing skills were superb. Certainly would recommend this to anyone especially people never having sailed before.

  4. ES

    Emily

    Sail in downtown Toronto

    We had an incredible trip on Dom's boat! We went out for my partner's birthday (2 of us). Dom is an amazing host and made us feel welcome from the start. He let us help with the sails and asked our input on where to go based on the wind. We had such a great experience and would recommend him to anyone!

  5. ZF

    Zachary

    Sail in downtown Toronto

    Captain Dom was an incredible host! If I could give 6/5 stars I would. He communication was excellent, he was welcoming, kind, safe and wanted to ensure we all got we needed when on board. His boat is excellent quality and we definitely got more than we asked for. 100% would recommend to anyone, and definitely will do again. Cheers!

  6. BB

    Barbara

    A Tropical Experience on a Massive Sailing Trimaran

    David was a most excellent captain. We were having a special send off for someone extremely important to us and David went above and beyond to make sure we all had a great time. He even got out his accordion and sang a song for the woman of the evening which was very funny and very special. We will absolutely book again. Thanks David and Sara!